The Key is in the Timing
by I'dRatherBeInStarsHollow
Summary: Rory discovers an old, unfinished letter as she sorts through her stuff before heading out on the campaign trail. Having broken up with Logan, there is nothing to stop her from finally finishing it. Set after the end of the show.
1. Chapter 1

**Rory discovers an old, unfinished letter as she sorts through her stuff before heading out on the campaign trail. Having broken up with Logan, there is nothing to stop her from finally finishing it. Set after the end of the show.**

****The characters aren't mine; they belong to Amy Sherman-Palladino.****

The Key is in the Timing

Rory hadn't expected going through her old things to be this hard. She had been away to Yale, to her grandparents' house and yet still, _still_, this house and this town and these memories had a hold on her that she was sure she would never really understand. Some of her stuff had been moved when the house was redone but thankfully, and possibly due more to Luke than to her mother, the boxes were neat and intuitively labeled.

She was surprised by how much stuff she had managed to collect over the years. She still had some mementos from her time with Dean in here (her box of cornstarch – the first, but sadly not the last, thing she had stolen). Even if things hadn't ended particularly well between them, the first time she fell in love and the boy she fell in love with would always have a place in her heart. It was as she was looking through this box (previously her Dean box but now labeled 'Personal' – another indicator of Luke's involvement as he, though he would never admit it of course, had never really warmed to Dean) that she stumbled across an old pad of paper, still partially filled with blank sheets. Why she hadn't used all the paper and how it could possibly be classed as 'personal', Rory didn't know. She it tossed away but, as sport had never been her strong point, instead of landing on the 'useful' pile on her bed, it slid back to the floor with the air lifting the cover as it did so.

Rory froze in shock. There were only two words on the first page. Two four-letter words which her brain didn't seem to understand.

_Dear Jess,_

That was it. Nothing else. Nothing offensive or shocking or particularly exciting… just 'Dear Jess'. This was the pad she had taken with her to DC that summer. And that had been the summer that she's realised she didn't love Dean anymore just as this was the summer she had realised she didn't love Logan anymore, or at least she couldn't be with Logan anymore. The parallels were striking. She wondered how Jess was; she hadn't spoken to him since their meeting, their kiss, at Truncheon. Was he mad? Sad? Great, now she was rhyming… The more she thought about it, the more desperate Rory became to finish the letter, one that she should have finished that summer before senior year but hadn't had the guts to. She wanted to believe she had the guts now.

_Dear Jess, _

_Hi. I know this really out of the blue and for that I'm sorry. I just… Jess, this is the letter I wrote to you the summer after I kissed you (well, I didn't write all of it then, just the 'Dear Jess' – for someone who says she's good with words, this letter sure did stump me). I just stumbled across it as I was packing up my things (I've got a job on Obama's campaign trail). I don't know why I didn't throw it out after we got together. I just forgot I guess._

_Anyway, I found the letter and I couldn't stop thinking about it and how I'd never finished it and how if I had finished it I might not have had to live through the painful Shane experience. I also couldn't stop thinking about parallels I'd noticed between my situation now and the situation then._

_I've broken up with Logan, Jess. He proposed to me but I couldn't say yes. Don't take this the wrong way: I'm not going to confess my love or anything and I'm not writing this to get you as my rebound; I'm just telling you what happened because I couldn't help but notice the recurring theme. Last time, I kissed you and went back to Dean. This time, I kissed you and went back to Logan. Both times, the relationships I went back to ended. _

_You're a recurring theme in my life, Jess. I wouldn't have this job or a degree without you and your re-occurring. So when I saw the letter, pathetic and unfinished, I knew you deserved better. You deserved a full letter with a beginning, middle and end. Maybe I'm the last person you want to hear from right now and I wouldn't blame you if I were. I just thought you deserved your letter – one with the truth._

_And I miss you, Jess. I probably shouldn't have written that but I'm not going to take it back now. You're getting the truth, mister._

_I'll include my address in case you want it. I hope you want it._

_Rory_

**A/N: Most of my ideas come to me as one shots but with this story I'm not sure whether to end it here or continue on with letters exchanged between Rory and Jess as she travels round the country – any thoughts or opinions would be much appreciated. Thanks.**


	2. Chapter 2

**A/N: Thank you for your support of this story in the comments etc. I hope you will be pleased by this next installment. As always, constructive feedback is appreciated if you have any.**

Chapter 2

_Dear Rory,_

_I don't know that you're the last person I wanted to hear from but, in the spirit of honesty, you're probably one of the last people I needed to hear from. I find it interesting that you noticed that parallel because I noticed it too Rory, the minute you walked out of that room. At least I get a letter, _the_ letter apparently, this time._

_So, Logan is gone. Logan is gone. Sorry, give me a minute for that to sink in; you did tell me that you were using me to get back at him because you loved him so I'm just trying to wrap my head around the details. I guess that was a while ago though._

_I can't be your second choice Rory, the exciting boy you kiss before running back to your normal life, not anymore. I know I made mistakes. I know I left you. But I can't just be that repeating pattern in your life: I can be a friend if that's what you want and I may as well let you know that my feelings haven't changed if that's what you want but I can't be something in between. I haven't got my life together for some complicated relationship to mess with that, even if the angst might help my writing. And Rory, I miss you too._

_Jess_

**A/N2: I realise Jess is quite open in this letter which could be seen as a little OC but I think that by now he might have grown enough to see the necessity of being open in order to be clear (especially because of what he's lost with Rory in the past due to lack of communication). Also, I feel Jess would be more articulate in writing than he ever would be in speech. Bearing this in mind, if you still get OC vibes, drop me a line and I'll know to work on it going forward.**


	3. Chapter 3

Chapter 3

_Dear Jess,_

_I'm sorry it has taken me so long to reply to your letter. I just needed some time to figure out answers for you and for myself. Plus, it's been getting pretty busy round here keeping up to date with everything._

_I've still had time to think about what you wrote though, plenty of it. I've only really just come out of a relationship Jess – that's not nothing – so it may take me some time to adjust. But finding that letter, finishing it, reading your reply… I really have missed you Jess. And, if this works for you, I'd like to keep writing letters to you with a view that this, us, we could become something more. I think I would like to be your girlfriend again Jess. I just need some time._

_So we write and we talk and at the end of my travels (or sooner if we can arrange it), when I'm back home, we talk about it properly, about everything; then we can see if this will work. I do want it to work Jess. Thoughts_

_Rory_


	4. Chapter 4

Chapter 4

_Dear Rory,_

_That sounds perfect to me._

_Jess_


	5. Chapter 5

Chapter 5

_Dear Jess,_

_I hope you know that you're infuriating. Although, when I opened your letter I did grin so wide that even my scatter-brained boss inquired as to whether as I was pregnant (apparently the woman who had my job before had been trying or something…). Sometimes I feel I don't know you at all anymore and then other times, like getting that stupid, one-sentence letter, I see you and me at seventeen. I know I have a lot to learn about us now and how we've changed but I like how I can see where we came from - like the sketch of a drawing ready to be filled in._

_Anyway, seeing as you think my idea was 'perfect', let's get this letter writing started. I mean, I know we've already been writing but you know Jess, you know what I mean. How are things at Truncheon? How's being an author? A published author no less?_

_Things are good here. Hectic. Time-consuming. All-encompassing. But good, Jess, really good._

_Luke and Mom are good too. In fact, they're definitely more than good. I don't know if Luke told you. I actually don't know how much you even talk to Luke anymore._

_Lane's a mom now. You remember her band? Well, she's now married to Zach and they have twin boys. I guess if you talk to Luke you might know that stuff. Coming up with stuff to write is tough, huh? I can see why stuck to that single sentence._

_Rory_


	6. Chapter 6

Chapter 6

_Rory,_

_I like that we can see where we came from, too. It's been something that I've clung too, really. When I came to see you at your grandparents' house, that's what I clung too – that even though you were now living in your grandparents' big house and not at Yale, you were the same Rory I'd fallen in love with. Same girl, different circumstances. And you're right about taking time to get to know each other again; you're right about most things. (But you can't keep using that or my calling your idea 'perfect' to your advantage)._

_The Truncheon's fine, Rory. The guys here are good guys, hardworking and frequently annoying but in an endearing kind of way. As for being an author, well, that mainly sinks in at three in the morning with the knowledge that my chapter deadline is four hours away and I haven't written a thing. It was easier with the first book; I always knew what I wanted to say and what came next because it had been in formation in my head for so long. I'm glad you're enjoying it out there – even if your boss hasn't registered that you're a different person. He will. You tend to make quite the impression on people._

_I do talk to Luke. Not all the time – we're not like you and your mom – but enough. Monthly, maybe. I'm glad things are sorting themselves out with Luke and your mom. He was really down for a while there._

_I had heard about Lane – yes from Luke. She does work at the diner after all. She picked the phone up once when I called and I could hear the distaste in her voice. I might have to do something about that if we're going to be thing._

_Speaking of people who don't like me, how are your grandparents (dare I ask…)?_

_Looking forward to your reply,_

_Jess_

**RIP Edward Herrman**


	7. Chapter 7

**A/N: Sorry it's been awhile - exams seem to lead to writer's block... I hope you enjoy.**

**Also, thanks to vfft for pointing the original formatting error. It should all be better now.**

Chapter 7

_Dear Jess,_

_I miss you Jess. Reading about you seeing me at my grandparents' was hard but it made me miss you all the more. I thought I was doing the right thing but you were the one who stepped up and saw that I wasn't okay, that I was letting petty things get in the way of my future. You were the one I listened to. And I miss having your voice around._

_It's good to hear about the Truncheon – in some ways it feels like another world I know little or nothing about. Another part of you I'm going to have to learn. That's okay, Jess, just weird sometimes, when the amount of stuff I don't know yet feels a little overwhelming. As for deadlines, you always did procrastinate but at least now you are getting the job done._

_I actually spoke to Lane about you today and you may be onto something with that whole dislike issue…She does say she's willing to have an open mind though. Still don't think it would hurt if you dropped her some flowers (or diapers… she needs diapers) next time you're in Stars Hollow... Also, I'm seeing Mom and Luke next week because we're heading back to DC before going north and they wanted to take a little romantic break so I'll say hi from you. I like that you and Luke are talking – you're good for each other whatever you might protest to the contrary._

_Yours,_

_Rory_


	8. Chapter 8

Chapter 8

_Dear Rory,_

_You do know that if you miss having my voice around you can call me, right? I know a phone call's not a letter but if you want my voice, it's right here waiting. And as for the Yale stuff, it was the least I could do._

_Just wondering if you didn't answer my question about your grandparents on purpose? I want you to know you can talk to me about them - that you can talk to me about anything really. _

_I'm glad to hear Lane's opening her mind to me - I may well follow up on that diaper idea though possibly through the post. I think maybe someone should warn Taylor next time I come into town. He's getting older and every time I see him I swear he seems one Jess-visit closer to an aneurism. _

_Have fun with your mom and Luke - I like that you and your mom are talking too. You're good for each other. In all seriousness though, I do like talking to Luke and I'm glad that I've let him back into my life (or more that he let me back into his)._

_I miss you too Rory._

_Jess_


	9. Chapter 9

Chapter 9

_Dear Jess, _

_I might just take you up on that phone call - that is if I get off at a sociable hour. I don't think you'd appreciate me calling you past midnight._

_I didn't mean not to talk about my grandparents; your question was just at the end of your letter and I was rushing to finish up my reply and send it off. Maybe it was subconscious though as I have been a little more distanced from them since I graduated. I feel bad because they didn't actually really do anything but they were quite disappointed when I turned Logan down. I think Mom's told them about us now as well so I may or may not have been avoiding having that particular conversation. To be fair to them, they seem to have accepted Luke, or at least they're trying, so maybe I shouldn't be so worried._

_I will make sure to let Taylor know next time you come to visit because as difficult as he is Stars Hollow wouldn't be Stars Hollow without him so avoiding an aneurism is probably wise._

_Mom and Luke enjoyed DC I think: Mom liked the food; Luke liked the Potomac and the bike trails. I felt really proud being able to show them around. I look forward to showing you around someday._

_Rory_


	10. Chapter 10

**Sorry once again for a formatting error on the original post and thanks to JItterbug5 for pointing it out.**

Chapter 10

"This is Jess Mariano."

"Jess?"

"Rory. Hi. You called."

"I did. This is weird. Isn't it weird?"

"It's not weird."

"Oh yeah?"

"Okay, it is a little weird."

"It's nice to hear your voice though."

"Yeah?"

"Yeah."

"How's DC?"

"It's good. It's calmed down a little. Everyone else is downstairs at the bar."

"And you're not?"

"I thought it could be a good time to call you."

"A much more worthwhile use of your time I'm sure."

"I would say so."

"So..."

"So."

"Rory."

"Jess."

"I'm going to be down is Stars Hollow in about a month."

"My Stars Hollow?"

"Is there another one?"

"How come?"

"Liz and TJ are throwing a birthday party for Doula. She reckons I should be there."

"That sounds nice."

"You would say that."

"I would and I did."

"Any chance you'll be around?"

"When is it?"

"I'll text you the details."

"Okay."

"So maybe I'll see you?"

"Even if you don't see me this time, you're definitely going to see me soon."

"See you soon then."

"See you soon."


	11. Chapter 11

_Dear Rory,_

_I'm really glad you called me yesterday and hope you can make it down to Stars Hollow (or I'll just have to figure out a way to come to DC, especially now you're offering to show me the sights). _

_I'm sorry things have been weird with your grandparents. Luke's told me that they're being better to him but I'm not going to pretend it the way they treat him doesn't hurt and worry me. I want this to work this time Rory and, whatever I think of your grandparents, I don't want you to lose any more of your relationship with them. I'll even be willing to come to Friday night dinner with you._

_Do you move on from DC anytime soon? And what's the place you're staying in like? I reckon it's probably better than the one-bed apartment I'm currently sharing with the new intern at the Truncheon, 'just 'til he gets on his feet'. You should see him, Ror. I'm going mad with him on my couch. Sorry to rant at you; I realise it's not that best way to end a letter. It's only that he's just started singing 'NSync songs so I'm trying to distract myself._

_Look forward to hearing from you and hope to see you soon._

_Jess_


	12. Chapter 12

Chapter 12

_Dear Jess,_

_I'm very sorry to hear about your intern… I can just imagine the two of you now. I can't promise I'm not laughing a little. We're actually moving on to New Hampshire in about a month - but not before a week's holiday that just happens to coincide with Doula's birthday. Who would have thought it? _

_The hotel I'm staying at is nice though not a patch on the Dragonfly obviously. I'm very comfortable and it's a good base to travel around DC from (the metro station is about five minutes away, three if I've had coffee)._

_Thank you for what you said about my grandparents. There will definitely be a Friday night dinner in the offing now I'm definitely coming to Stars Hollow and it would mean a lot to have your support. I lost a lot of what I thought I believed while staying at that house and I didn't really process any of it until I got away from it, out here on the campaign trail, which had meant I haven't really faced a lot of it. I know my grandparents can be difficult but they do mean well (except maybe in Luke's case when he and mom were first dating…). I know they're trying._

_I can't wait to see you Jess. I cam't quite believe any of this is real._

_Rory_


	13. Chapter 13

Chapter 13

_Dear Rory,_

_My intern is no problem now I know I have seeing you to look forward to (even if that prospect is marred by the idea of Friday night dinner - I seem to recall our last one not going so well)._

_Hopefully the week in Stars Hollow will give you the time you need, without your grandparents, or Logan, or me if you need it. This whole thing - us, these letters - has been surreal (long may they continue!). I didn't realise how much I missed you, Rory, and now I can think about you and it be allowed: no hiding, no pretending... Knowing that I'm going to see you soon just makes me miss you more._

_Make sure you've let Taylor know I'm coming; we're going to take that town by storm._

_Love,_

_Jess_

**A/N: This is the end of The Key is in the Timing - but not the end of this story. I wanted to keep this fic as just letters (and a phone call) but I will be writing the story of Rory and Jess meeting in Stars Hollow for any of you who'd like to read it (and for my own enjoyment/wish fulfilment). Thanks for your support and I hope you've liked this :)**


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